Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 05:54:00 UTC |
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Update Date | 2016-11-09 01:21:20 UTC |
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Accession Number | CHEM035579 |
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Identification |
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Common Name | Epsilon-(gamma-Glutamyl)-lysine |
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Class | Small Molecule |
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Description | An N(6)-acyl-L-lysine derivative in which the acyl group is specified as gamma-glutamyl. |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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epsilon-(gamma-L-Glutamyl)-L-lysine | ChEBI | epsilon-(L-gamma-Glutamyl)-L-lysine | ChEBI | gamma-Glu-epsilon-lys | ChEBI | gamma-Glutamyl-epsilon-lysine | ChEBI | L-gamma-Glutamyl-L-epsilon-lysine | ChEBI | N(6)-L-gamma-Glutamyl-L-lysine | ChEBI | N(epsilon)-(gamma-Glutamyl)-lysine | ChEBI | epsilon-(g-L-Glutamyl)-L-lysine | Generator | epsilon-(L-g-Glutamyl)-L-lysine | Generator | g-Glu-epsilon-lys | Generator | g-Glutamyl-epsilon-lysine | Generator | L-g-Glutamyl-L-epsilon-lysine | Generator | N(6)-L-g-Glutamyl-L-lysine | Generator | N(epsilon)-(g-Glutamyl)-lysine | Generator | epsilon-(g-Glutamyl)lysine | Generator | epsilon-(gamma-Glu)-lys | HMDB, MeSH | epsilon-(gamma-Glutamyl)lysine | HMDB | epsilon-(gamma-Glutamyl)lysine isodipeptide | HMDB, MeSH | GGEL peptide | MeSH, HMDB | N-epsilon-(gamma-L-Glutamyl)lysine | MeSH, HMDB | epsilon-(gamma-Glutamyl)-lysine | MeSH, HMDB | Epsilon-(g-Glutamyl)-lysine | Generator, HMDB | N6-L-gamma-Glutamyl-L-lysine | HMDB | N6-L-γ-Glutamyl-L-lysine | HMDB | Nepsilon(gamma-Glutamyl)lysine | HMDB | Nepsilon-(gamma-Glutamyl)-L-lysine | HMDB | Nε(γ-Glutamyl)lysine | HMDB | Nε-(γ-Glutamyl)-L-lysine | HMDB | epsilon-(gamma-L-Glutamyl)lysine | HMDB | epsilonN-(gamma-L-Glutamyl)-L-lysine | HMDB | γ-Glutamyl-ε-lysine | HMDB | ε-(L-γ-Glutamyl)-L-lysine | HMDB | ε-(γ-Glutamyl)lysine | HMDB | ε-(γ-L-Glutamyl)-L-lysine | HMDB | ε-(γ-L-Glutamyl)lysine | HMDB | εN-(γ-L-Glutamyl)-L-lysine | HMDB |
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Chemical Formula | C11H21N3O5 |
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Average Molecular Mass | 275.302 g/mol |
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Monoisotopic Mass | 275.148 g/mol |
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CAS Registry Number | 17105-15-6 |
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IUPAC Name | (2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid |
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Traditional Name | N(6)-L-gamma-glutamyl-L-lysine |
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SMILES | N[C@@H](CCCCNC(=O)CC[C@H](N)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 |
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InChI Key | JPKNLFVGUZRHOB-YUMQZZPRSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Glutamine and derivatives |
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Alternative Parents | |
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Substituents | - Glutamine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Medium-chain fatty acid
- Amino fatty acid
- Dicarboxylic acid or derivatives
- Fatty acyl
- Fatty acid
- Fatty amide
- N-acyl-amine
- Carboxamide group
- Carboxylic acid salt
- Amino acid
- Secondary carboxylic acid amide
- Carboxylic acid
- Organooxygen compound
- Organonitrogen compound
- Organic zwitterion
- Primary aliphatic amine
- Organic salt
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Primary amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-5940000000-d882bed3b5529ecff7f9 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0udi-6639100000-f6ca1e086349e3426243 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0490000000-072f36ed9a7b3013d059 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-2930000000-392395a44df2ae8037f8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9500000000-6e7ed98ff09e19e298dc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05fr-0190000000-58b6ca56f7cccfc512be | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0aba-1690000000-fc6b7fb17538a52f8f98 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006w-9700000000-4409c236d141d5814427 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05fr-0190000000-87a26493d0e45ab09e99 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-1930000000-3595f6a3ff829eac51de | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9500000000-8574eb2f5fa536d0c5ab | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0059-0390000000-6d00013244e4fc3d3d9b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-9430000000-86b20a12b25ddf059e72 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9200000000-6238074e2599c8441ec5 | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0003869 |
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FooDB ID | FDB023239 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 5378717 |
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ChEBI ID | 88494 |
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PubChem Compound ID | 7015684 |
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Kegg Compound ID | Not Available |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Jeitner TM, Bogdanov MB, Matson WR, Daikhin Y, Yudkoff M, Folk JE, Steinman L, Browne SE, Beal MF, Blass JP, Cooper AJ: N(epsilon)-(gamma-L-glutamyl)-L-lysine (GGEL) is increased in cerebrospinal fluid of patients with Huntington's disease. J Neurochem. 2001 Dec;79(5):1109-12. | 2. El Nahas AM, Abo-Zenah H, Skill NJ, Bex S, Wild G, Griffin M, Johnson TS: Elevated epsilon-(gamma-glutamyl)lysine in human diabetic nephropathy results from increased expression and cellular release of tissue transglutaminase. Nephron Clin Pract. 2004;97(3):c108-17. | 3. Andringa G, Lam KY, Chegary M, Wang X, Chase TN, Bennett MC: Tissue transglutaminase catalyzes the formation of alpha-synuclein crosslinks in Parkinson's disease. FASEB J. 2004 May;18(7):932-4. Epub 2004 Mar 4. | 4. Priglinger SG, Alge CS, Kook D, Thiel M, Schumann R, Eibl K, Yu A, Neubauer AS, Kampik A, Welge-Lussen U: Potential role of tissue transglutaminase in glaucoma filtering surgery. Invest Ophthalmol Vis Sci. 2006 Sep;47(9):3835-45. | 5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. |
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